Potassium Carbonate → Tert-butyl (3-methyl-4-((5-nitropyridin-2-yl)oxy)phenyl)carbamate

HRID 1844509Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:6](=[O:16])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:12][C:11]=1[O:14][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF (50 ml) solution of tert-butyl(4-hydroxy-3-methylphenyl)carbamate (5.00 g) was added 2-chloro-5-nitropyridine (3.91 g) and potassium carbonate (4.64 g). After stirring at 80° C. for 4 hours, the mixture was concentrated under reduced pressure. The residue was diluted in AcOEt and water, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure. To the residue were added Et2O and the mixture was stirred at room temperature for 2 hours. The resulting precipitate was collected by filtration to afford the title compound (6.04 g) as a brown powder.

Workup

concentrationthe mixture was concentrated under reduced pressure
additionThe residue was diluted in AcOEt
extractionwater, and extracted with AcOEt
washThe organic layer was washed with water, saturated aqueous NaCl
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
additionTo the residue were added Et2O
stirringthe mixture was stirred at room temperature for 2 hours
filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-60458a703f4a4db5855e1a418eb427f7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946437B2

Reaction notes

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